20,150

Middletown, DE Homes

Section Image Section Image
  • 556 Lewes Landing Rd, Middletown, DE 19709
    556 Lewes Landing Rd, Middletown, DE 19709
    556 Lewes Landing Rd, Middletown, DE 19709
    /27

    $489,000 Sold Nov 03, 2025

    556 Lewes Landing Rd, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 2,335 Sq Ft
    • Built 2023

    Last Sold Summary

    • $209/SF
    • 15 Days On Market

    Current Estimated Value $470,652

    Last Listing Agent Suzanne Garcia Myers Realty

    556 Lewes Landing Rd, Middletown, DE 19709
    • 916 Benalli Dr, Middletown, DE 19709
      916 Benalli Dr, Middletown, DE 19709
      916 Benalli Dr, Middletown, DE 19709
      /56

      Est $679,768 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,615 Sq Ft

      916 Benalli Dr, Middletown, DE 19709

      916 Benalli Dr, Middletown, DE 19709
  • 530 Longhorn Loop, Middletown, DE 19709
    530 Longhorn Loop, Middletown, DE 19709
    530 Longhorn Loop, Middletown, DE 19709
    /11

    $748,262 Pending

    • 3 Beds
    • 2 Baths
    • 3,377 Sq Ft

    530 Longhorn Loop, Middletown, DE 19709

    Welcome to the Cottonwood Model, TO BE BUILT, in the highly sought-after 55+ community of Traditions at Whitehall. This 3-bedroom home features a generous Owner’s Suite at the front of the home, complete with double walk-in closets leading to a luxurious en-suite bath, offering a privacy water closet and a 5-foot tile shower. At the rear of the home, you will find the kitchen and dining area that

    Lindsay Shaffer RE/MAX Elite

    530 Longhorn Loop, Middletown, DE 19709
  • 843 New Castle Landing Dr, Middletown, DE 19709
    843 New Castle Landing Dr, Middletown, DE 19709
    /2

    $742,790 Sold Nov 23, 2025

    843 New Castle Landing Dr, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 2,925 Sq Ft
    • Built 2025

    Last Sold Summary

    • $254/SF

    Last Listing Agent Gina-lynn Rubin Toll Brothers Real Estate, Inc.

    843 New Castle Landing Dr, Middletown, DE 19709
    • 209 Snow Goose Dr, Middletown, DE 19709
      209 Snow Goose Dr, Middletown, DE 19709
      209 Snow Goose Dr, Middletown, DE 19709
      /66

      Est $625,047 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,825 Sq Ft

      209 Snow Goose Dr, Middletown, DE 19709

      209 Snow Goose Dr, Middletown, DE 19709
  • 513 Spring Hollow Dr, Middletown, DE 19709
    513 Spring Hollow Dr, Middletown, DE 19709
    513 Spring Hollow Dr, Middletown, DE 19709
    /75

    $779,999 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 4,350 Sq Ft

    513 Spring Hollow Dr, Middletown, DE 19709

    Welcome to 513 Spring Hollow Drive, located in the sought after neighborhood of PARKSIDE where manicured lawns, breathtaking Grand entrances.... that shout our pure elegance and landscaped open areas that are where you can imagine your family loving where they live. This stunning Semi Custom home in situated on a great corner lot that is across from the Parkside Community Clubhouse, pool, fitness

    Ann Marie Germano Patterson-Schwartz-Middletown

    513 Spring Hollow Dr, Middletown, DE 19709
  • 189 Gillespie Ave, Middletown, DE 19709
    189 Gillespie Ave, Middletown, DE 19709
    189 Gillespie Ave, Middletown, DE 19709
    /68

    $325,000 Sold Jan 27, 2026

    189 Gillespie Ave, Middletown, DE 19709

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 2005

    Last Sold Summary

    • $176/SF
    • 72 Days On Market

    Last Listing Agent Peggy Sheehan Patterson-Schwartz-Middletown

    189 Gillespie Ave, Middletown, DE 19709
    • 217 Snow Goose Dr, Middletown, DE 19709
      217 Snow Goose Dr, Middletown, DE 19709
      217 Snow Goose Dr, Middletown, DE 19709
      /83

      Est $659,303 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,613 Sq Ft

      217 Snow Goose Dr, Middletown, DE 19709

      217 Snow Goose Dr, Middletown, DE 19709
  • 126 Green Forest Dr Unit 5 HOUSTON, Middletown, DE 19709
    126 Green Forest Dr Unit 5 HOUSTON, Middletown, DE 19709
    126 Green Forest Dr Unit 5 HOUSTON, Middletown, DE 19709
    /44

    $685,000 Open Mon 8AM - 8PM

    • 4 Beds
    • 2.5 Baths
    • 3,368 Sq Ft

    126 Green Forest Dr Unit 5 HOUSTON, Middletown, DE 19709

    Last lots available. 7 month build time. See this model any day through the NTernow app. Rothwell Estates from Benchmark Builders. The HOUSTON (to be built) is our main decorated model. The 2 story foyer & great room, and a 2nd floor bridge are some of the stand out features in this home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich

    Lindsay Shaffer RE/MAX Elite

    126 Green Forest Dr Unit 5 HOUSTON, Middletown, DE 19709
  • 202 Douglas Way, Middletown, DE 19709
    202 Douglas Way, Middletown, DE 19709
    202 Douglas Way, Middletown, DE 19709
    /17

    $435,000 Sold Feb 17, 2025

    202 Douglas Way, Middletown, DE 19709

    • 3 Beds
    • 4 Baths
    • 2,295 Sq Ft
    • Built 2023

    Last Sold Summary

    • $190/SF
    • 377 Days On Market

    Current Estimated Value $461,971

    Last Listing Agent Barbara Heilman Delaware Homes Inc

    202 Douglas Way, Middletown, DE 19709
    • 644 Nesting Ln, Middletown, DE 19709
      644 Nesting Ln, Middletown, DE 19709
      644 Nesting Ln, Middletown, DE 19709
      /101

      Est $783,153 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 3,950 Sq Ft

      644 Nesting Ln, Middletown, DE 19709

      644 Nesting Ln, Middletown, DE 19709
  • 25 Franklin Dr, Middletown, DE 19709
    25 Franklin Dr, Middletown, DE 19709
    25 Franklin Dr, Middletown, DE 19709
    /23

    $339,900

    • 3 Beds
    • 1.5 Baths
    • 1,325 Sq Ft

    25 Franklin Dr, Middletown, DE 19709

    Must-see, move-in-ready home in Middletown, located in the Great Appoquinimink School District. This 3-bedroom, 2-bath property was fully updated in 2018 and offers an open concept layout designed for everyday living and entertaining. The main level features a dining area, an eat-in kitchen with granite countertops, and a spacious living room. A sliding glass door fills the space with natural

    Bob Comegys EXP Realty, LLC

    25 Franklin Dr, Middletown, DE 19709
  • 16 E Shakespeare Dr, Middletown, DE 19709
    16 E Shakespeare Dr, Middletown, DE 19709
    16 E Shakespeare Dr, Middletown, DE 19709
    /43

    $584,000 Sold Dec 30, 2025

    16 E Shakespeare Dr, Middletown, DE 19709

    • 5 Beds
    • 3.5 Baths
    • 2,725 Sq Ft
    • Built 2004

    Last Sold Summary

    • $214/SF
    • 84 Days On Market

    Last Listing Agent Gary Stewart Century 21 Emerald

    16 E Shakespeare Dr, Middletown, DE 19709
    • 213 Tory St, Middletown, DE 19709
      213 Tory St, Middletown, DE 19709
      213 Tory St, Middletown, DE 19709
      /53

      Est $779,998 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 4,200 Sq Ft

      213 Tory St, Middletown, DE 19709

      213 Tory St, Middletown, DE 19709
  • 204 Baldy Ln Unit 36490855, Middletown, DE 19709
    204 Baldy Ln Unit 36490855, Middletown, DE 19709
    204 Baldy Ln Unit 36490855, Middletown, DE 19709
    /46

    $579,000 New Construction

    • 3 Beds
    • 2 Baths
    • 2,004 Sq Ft

    Cayot Plan at Traditions at Whitehall - 55+ Active Adult - Single Family, Middletown, DE 19709

    Cayot Stylish Comfort with Plenty of Space The Cayot offers 2,004 sq. ft. of well-designed living, featuring 3 bedrooms and 2 baths, including a main-level owners suite for easy, one-floor living. The open-concept kitchen and great room make entertaining a breeze, while the two-car rear-entry garage adds convenience. This home combines functionality and style perfectly for active adults who want

    Benchmark Builders Builder
    204 Baldy Ln Unit 36490855, Middletown, DE 19709
  • 10 Morning Dew Dr, Middletown, DE 19709
    10 Morning Dew Dr, Middletown, DE 19709
    10 Morning Dew Dr, Middletown, DE 19709
    /24

    $515,000 Sold Feb 28, 2025

    10 Morning Dew Dr, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 3,250 Sq Ft
    • Built 2000

    Last Sold Summary

    • $158/SF
    • 21 Days On Market

    Current Estimated Value $526,401

    Last Listing Agent Evan Ward ELM Properties

    10 Morning Dew Dr, Middletown, DE 19709
    • 240 Tory St, Middletown, DE 19709
      240 Tory St, Middletown, DE 19709
      240 Tory St, Middletown, DE 19709
      /44

      Est $746,371 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,625 Sq Ft

      240 Tory St, Middletown, DE 19709

      240 Tory St, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
    /23

    $464,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,443 Sq Ft

    Taylor Plan at Venue at Winchelsea 55+ - Winchelsea Towns, Middletown, DE 19709

    This new two-story townhome is designed to promote low-maintenance living with a sophisticated twist. On the first floor is everything you need day-to-day, featuring a private owner’s suite, a convenient study and an open-concept layout shared among the kitchen, dining room and spacious family room. The top floor presents a loft and two versatile bedrooms to customize as homeowners see fit.

    Lennar Builder
    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
  • 407 Northhampton Way, Middletown, DE 19709
    407 Northhampton Way, Middletown, DE 19709
    407 Northhampton Way, Middletown, DE 19709
    /77

    $550,000 Sold Aug 28, 2025

    407 Northhampton Way, Middletown, DE 19709

    • 4 Beds
    • 3.5 Baths
    • 3,523 Sq Ft
    • Built 2008

    Last Sold Summary

    • $156/SF
    • 19 Days On Market

    Current Estimated Value $551,769

    Last Listing Agent Michelle Brown EXP Realty, LLC

    407 Northhampton Way, Middletown, DE 19709
    • 254 E Crail Ct, Middletown, DE 19709
      254 E Crail Ct, Middletown, DE 19709
      254 E Crail Ct, Middletown, DE 19709
      /78

      Est $766,280 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 4,400 Sq Ft

      254 E Crail Ct, Middletown, DE 19709

      254 E Crail Ct, Middletown, DE 19709
  • 400 Rederick Ln Unit 36457195, Middletown, DE 19709
    400 Rederick Ln Unit 36457195, Middletown, DE 19709
    400 Rederick Ln Unit 36457195, Middletown, DE 19709
    /3

    $582,500 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,589 Sq Ft

    Oxford Plan at Ponds of Odessa - Single Family Homes, Middletown, DE 19709

    Large open-concept floor plan, 4 bedrooms, 2.5 baths, airy 2 stories. Tours by appointment onlyplease call 302-865-0759 to schedule. Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    400 Rederick Ln Unit 36457195, Middletown, DE 19709
  • 540 Swansea Dr, Middletown, DE 19709
    540 Swansea Dr, Middletown, DE 19709
    540 Swansea Dr, Middletown, DE 19709
    /37

    $629,900 Sold Sep 03, 2025

    540 Swansea Dr, Middletown, DE 19709

    • 5 Beds
    • 3.5 Baths
    • 4,447 Sq Ft
    • Built 2018

    Last Sold Summary

    • $142/SF
    • 16 Days On Market

    Current Estimated Value $629,003

    Last Listing Agent Deborah Cadwallader RE/MAX Horizons

    540 Swansea Dr, Middletown, DE 19709
    • 251 E Crail Ct, Middletown, DE 19709
      251 E Crail Ct, Middletown, DE 19709
      251 E Crail Ct, Middletown, DE 19709
      /48

      Est $680,288 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,812 Sq Ft

      251 E Crail Ct, Middletown, DE 19709

      251 E Crail Ct, Middletown, DE 19709
  • 1102 Highland St, Middletown, DE 19709
    1102 Highland St, Middletown, DE 19709
    1102 Highland St, Middletown, DE 19709
    /14

    $504,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,794 Sq Ft

    1102 Highland St, Middletown, DE 19709

    Photos shown are of a previously built Oxford model and are for illustrative purposes only. Features, finishes, and layout may vary in the actual home.

    Benchmark Builders Builder
    1102 Highland St, Middletown, DE 19709
  • 207 Serenity Ln, Middletown, DE 19709
    207 Serenity Ln, Middletown, DE 19709
    207 Serenity Ln, Middletown, DE 19709
    /33

    $650,000 Sold Jun 13, 2025

    207 Serenity Ln, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 3,100 Sq Ft
    • Built 2023

    Last Sold Summary

    • $210/SF
    • 1 Day On Market

    Current Estimated Value $659,593

    Last Listing Agent Eric Buck Long & Foster Real Estate, Inc.

    207 Serenity Ln, Middletown, DE 19709
    • 205 E Crail Ct, Middletown, DE 19709
      205 E Crail Ct, Middletown, DE 19709
      205 E Crail Ct, Middletown, DE 19709
      /90

      Est $658,576 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,425 Sq Ft

      205 E Crail Ct, Middletown, DE 19709

      205 E Crail Ct, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
    /22

    $524,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,936 Sq Ft

    Mendocino Plan at Venue at Winchelsea 55+ - Winchelsea Singles, Middletown, DE 19709

    This single-story home is designed to offer comfort and luxury at the same time. Off the foyer is a flex space for versatile uses and a formal dining room, followed by an open concept main living area with backyard access. In addition to the expansive owner’s suite with a private full-sized bathroom, there is a secondary bedroom that can be used for overnight guests or personal needs. A two-car

    Lennar Builder
    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
  • 47 Spring Arbor Dr, Middletown, DE 19709
    47 Spring Arbor Dr, Middletown, DE 19709
    47 Spring Arbor Dr, Middletown, DE 19709
    /41

    $475,000 Sold Dec 01, 2025

    47 Spring Arbor Dr, Middletown, DE 19709

    • 2 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 20 Days On Market

    Last Listing Agent Rick Anibal RE/MAX Advantage Realty

    47 Spring Arbor Dr, Middletown, DE 19709
    • 211 E Crail Ct, Middletown, DE 19709
      211 E Crail Ct, Middletown, DE 19709
      211 E Crail Ct, Middletown, DE 19709
      /26

      Est $682,061 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,875 Sq Ft

      211 E Crail Ct, Middletown, DE 19709

      211 E Crail Ct, Middletown, DE 19709
  • 251 Dillon Cir, Middletown, DE 19709
    251 Dillon Cir, Middletown, DE 19709
    251 Dillon Cir, Middletown, DE 19709
    /56

    $1,049,000

    • 4 Beds
    • 4 Baths
    • 4,725 Sq Ft

    251 Dillon Cir, Middletown, DE 19709

    Presenting a distinguished 4-bedroom, 4 full-bathroom, Colorado II model in Summit Pointe, a newly built boutique community, crafted by K. Hovnanian Homes. This property, only 31⁄2 years old, offers 4,725 square feet of living space with an expanded floor plan (please refer to the attached floor plans, noting the upgraded, extended areas marked in blue), with a primarily brick front elevation.

    Sally Bittel Thomas Compass

    251 Dillon Cir, Middletown, DE 19709
  • 2218 S Okeeffe Ln, Middletown, DE 19709
    2218 S Okeeffe Ln, Middletown, DE 19709
    2218 S Okeeffe Ln, Middletown, DE 19709
    /42

    $490,000 Sold May 01, 2025

    2218 S Okeeffe Ln, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 2,675 Sq Ft
    • Built 2014

    Last Sold Summary

    • $183/SF
    • 4 Days On Market

    Current Estimated Value $494,733

    Last Listing Agent Daniel Marcantuno Keller Williams Real Estate - West Chester

    2218 S Okeeffe Ln, Middletown, DE 19709
    • 2 Lomond Ln, Middletown, DE 19709
      2 Lomond Ln, Middletown, DE 19709
      2 Lomond Ln, Middletown, DE 19709
      /65

      Est $820,964 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 5,750 Sq Ft

      2 Lomond Ln, Middletown, DE 19709

      2 Lomond Ln, Middletown, DE 19709
  • 204 Baldy Ln Unit BELVILLE, Middletown, DE 19709
    204 Baldy Ln Unit BELVILLE, Middletown, DE 19709
    204 Baldy Ln Unit BELVILLE, Middletown, DE 19709
    /13

    $521,500 Open Sun 11AM - 5PM

    • 2 Beds
    • 2 Baths
    • 2,059 Sq Ft

    204 Baldy Ln Unit BELVILLE, Middletown, DE 19709

    Welcome to the Belville Model in the 55+community of Traditions at Whitehall. TO BE BUILT. This inviting 2-Bedroom home has a welcoming foyer which leads you down the hall towards the main living area! An open kitchen and breakfast area which flows into the large great room and is perfect for entertaining! The owner’s suite in the front features a large walk-in closet and owner’s bath with a

    Lindsay Shaffer RE/MAX Elite

    204 Baldy Ln Unit BELVILLE, Middletown, DE 19709
  • 198 Gloucester Blvd, Middletown, DE 19709
    198 Gloucester Blvd, Middletown, DE 19709
    198 Gloucester Blvd, Middletown, DE 19709
    /30

    $535,000 Sold Feb 20, 2025

    198 Gloucester Blvd, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 4,523 Sq Ft
    • Built 2009

    Last Sold Summary

    • $118/SF
    • 19 Days On Market

    Current Estimated Value $565,043

    Last Listing Agent Shakima Thimba Patterson-Schwartz-Middletown

    198 Gloucester Blvd, Middletown, DE 19709
    • 42 W Kilts Ln, Middletown, DE 19709
      42 W Kilts Ln, Middletown, DE 19709
      42 W Kilts Ln, Middletown, DE 19709
      /37

      Est $644,079 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,875 Sq Ft

      42 W Kilts Ln, Middletown, DE 19709

      42 W Kilts Ln, Middletown, DE 19709
  • 148 Gazebo Ln, Middletown, DE 19709
    148 Gazebo Ln, Middletown, DE 19709
    148 Gazebo Ln, Middletown, DE 19709
    /45

    $490,000

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    148 Gazebo Ln, Middletown, DE 19709

    WOW! Simply Gorgeous! This popular Kipling model offers open floor plan, foyer with 11 FT ceiling, wainscoting and gleaming hardwoods extending from foyer thru living room, dining room and kitchen. Well appointed kitchen has granite counters including island with seating for 3, stainless steel appliances, recessed & upgraded lighting. Dining area has sliders to upgraded & enlarged paver patio,

    Mary Lynch Patterson-Schwartz-Middletown

    148 Gazebo Ln, Middletown, DE 19709
  • 878 Sweet Birch Dr, Middletown, DE 19709
    878 Sweet Birch Dr, Middletown, DE 19709
    878 Sweet Birch Dr, Middletown, DE 19709
    /97

    $960,000 Sold Jul 28, 2025

    878 Sweet Birch Dr, Middletown, DE 19709

    • 6 Beds
    • 5 Baths
    • 5,250 Sq Ft
    • Built 2020

    Last Sold Summary

    • $183/SF
    • 9 Days On Market

    Current Estimated Value $974,571

    Last Listing Agent Ann Marie Germano Patterson-Schwartz-Middletown

    878 Sweet Birch Dr, Middletown, DE 19709
    • 712 Pergola Ln, Middletown, DE 19709
      712 Pergola Ln, Middletown, DE 19709
      712 Pergola Ln, Middletown, DE 19709
      /40

      Est $532,164 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 2,450 Sq Ft

      712 Pergola Ln, Middletown, DE 19709

      712 Pergola Ln, Middletown, DE 19709
  • 1930 Dixon Way, Middletown, DE 19709
    1930 Dixon Way, Middletown, DE 19709
    1930 Dixon Way, Middletown, DE 19709
    /34

    $554,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,833 Sq Ft

    1930 Dixon Way, Middletown, DE 19709

    The Asheville - with over 2,800 finished sq. ft. - delivers modern design and comfortable living with spaces made for both entertaining and everyday relaxation. The contemporary kitchen is the heart of the home, featuring a large island, walk-in pantry, and designer Looks interior selections that elevate the space. A covered front porch and rear deck invite you to welcome guests or unwind

    Barbara Heilman Delaware Homes Inc

    1930 Dixon Way, Middletown, DE 19709
  • 932 Lissicasey Loop, Middletown, DE 19709
    932 Lissicasey Loop, Middletown, DE 19709
    932 Lissicasey Loop, Middletown, DE 19709
    /40

    $412,000 Sold Jan 23, 2026

    932 Lissicasey Loop, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Built 2018

    Last Sold Summary

    • $196/SF
    • 28 Days On Market

    Last Listing Agent Emma Stricker First Class Properties

    932 Lissicasey Loop, Middletown, DE 19709

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